Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801003592/na6052sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801003592/na6052Isup2.hkl |
CCDC reference: 159836
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.021 Å
- R factor = 0.064
- wR factor = 0.186
- Data-to-parameter ratio = 15.7
checkCIF results
No syntax errors found
Alert Level B:
PLAT_111 Alert B ADDSYM detects (pseudo) centre of symmetry ... 96 Perc Fit PLAT_112 Alert B ADDSYM detects additional (pseudo)symmetry ... ? PLAT_113 Alert B ADDSYM suggests Pseudo/New Spacegroup ........ P21/c
Alert Level C:
PLAT_202 Alert C Isotropic non-H Atoms in Anion/Solvent = 10 PLAT_213 Alert C Atom O5 has ADP max/min Ratio ........... 3.10 PLAT_213 Alert C Atom C51 has ADP max/min Ratio ........... 3.50 PLAT_420 Alert C D-H Without Acceptor O(9) - H(9B) ? PLAT_702 Alert C Angle Calc 119.7(15), Rep 118.0(10), Dev. 1.13 Sigma C66 -C67 -C68 1.555 1.555 1.555 PLAT_721 Alert C Bond Calc 0.92148, Rep 0.91100, Dev. 0.01 Ang. C48 -H48A 1.555 1.555 PLAT_721 Alert C Bond Calc 0.93342, Rep 0.94400, Dev. 0.01 Ang. C70 -H70C 1.555 1.555 PLAT_722 Alert C Angle Calc 116.11, Rep 115.00, Dev. 1.11 Degree C27 -C26 -H26 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 110.09, Rep 109.00, Dev. 1.09 Degree H31B -C31 -H31C 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 119.26, Rep 118.00, Dev. 1.26 Degree C46 -C45 -H45 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 109.20, Rep 108.00, Dev. 1.20 Degree C44 -C48 -H48B 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 109.63, Rep 108.00, Dev. 1.63 Degree C44 -C48 -H48C 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 109.25, Rep 108.00, Dev. 1.25 Degree C50 -C51 -H51B 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 110.09, Rep 109.00, Dev. 1.09 Degree C53 -C61 -H61A 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 111.35, Rep 110.00, Dev. 1.35 Degree H63A -C63 -H63C 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 119.17, Rep 118.00, Dev. 1.17 Degree C67 -C66 -H66 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 118.13, Rep 117.00, Dev. 1.13 Degree C67 -C68 -H68 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 119.40, Rep 118.00, Dev. 1.40 Degree C69 -C68 -H68 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 111.32, Rep 110.00, Dev. 1.32 Degree H70B -C70 -H70C 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 111.59, Rep 110.00, Dev. 1.59 Degree H71B -C71 -H71C 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 110.10, Rep 109.00, Dev. 1.10 Degree C69 -C72 -H72A 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 109.23, Rep 108.00, Dev. 1.23 Degree C69 -C72 -H72B 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 119.39, Rep 118.00, Dev. 1.39 Degree C76 -C75 -H75 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 118.12, Rep 117.00, Dev. 1.12 Degree C78 -C77 -H77 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 110.33, Rep 109.00, Dev. 1.33 Degree C74 -C79 -H79B 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 109.13, Rep 108.00, Dev. 1.13 Degree C82 -C83 -H83C 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 110.12, Rep 109.00, Dev. 1.12 Degree H84B -C84 -H84C 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 110.24, Rep 109.00, Dev. 1.24 Degree C85 -C86 -H86A 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 109.01, Rep 108.00, Dev. 1.01 Degree C87 -C86 -H86A 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 109.23, Rep 108.00, Dev. 1.23 Degree H86A -C86 -H86B 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 112.15, Rep 111.00, Dev. 1.15 Degree C88 -C87 -H87A 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 112.30, Rep 111.00, Dev. 1.30 Degree C88 -C87 -H87B 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 109.70, Rep 108.00, Dev. 1.70 Degree H89A -C89 -H89B 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 108.07, Rep 107.00, Dev. 1.07 Degree C92 -C91 -H91A 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 117.30, Rep 116.00, Dev. 1.30 Degree C91 -C92 -H92A 1.555 1.555 1.555 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 11744 Count of symmetry unique reflns 8578 Completeness (_total/calc) 136.91% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3166 Fraction of Friedel pairs measured 0.369 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
3 Alert Level B = Potential problem
35 Alert Level C = Please check
The chiral tetradentate ligand (-)-L [L = 1,2-bis(2,4,6-trimethylphenyl)ethane-1,2-diylbis(nitrilomethylidyne)]- bis(pentane-2,4-dione)] was derived from optically pure (+)-1,2-bis(2,4,6-trimethylphenyl)ethylenediamine, which was prepared according to the literature (Roskamp & Pedersen, 1987; Zhang, 1991). Optical resolution of the racemic diamine with (-)-mandelic acid led to optically pure (+)-diamine. The specific rotation of the ligand L and its original diamine, [α]D at 300 K, are -186° (c = 1.02, CHCl3) and +200 ° (c = 1.19, CH2Cl2), respectively. Optical purities of the ligand L and the diamine were determined using Daicel Chiralpak AD (hexane/2-propanol = 80/20, hexane/ethanol/diethylamine = 90/10/0.1, respectively). The title complex was synthesized as described previously (Yamada et al., 1999). To a solution of the ligand (-)-L in methanol were added an aqueous solution of sodium hydroxide and an aqueous solution of cobalt(II) chloride hexahydrate at 323 K under nitrogen bubbling. The cobalt(II) complex precipitated in the red–violet solution as an orange solid. This complex was oxidized to the bromocobalt(III) complex by adding bromine in CH2Cl2 under a nitrogen atmosphere. The crystals of (I) were grown from a tetrahydrofuran (THF) solution by diffusion of a little amount of hexane. The crystal specimen was sealed in a capillary to avoid efflorescence. The specific rotation [α]D of the title Co complex at 300 K is -1440° (c = 0.022, THF).
Friedel pairs were measured for the reflections with θ < 20°. The positional parameters of the aqua H atoms were calculated geometrically (assuming the sp2 hybridization) based on the corresponding peaks on difference syntheses. The other H-atom positional parameters were also calculated and fixed with Uiso(H) = 1.2Ueq(parent atom). The non-H atoms of THF molecules (the O15–O16 and C85–C92 atoms) were refined isotropically with restraints of C—C = 1.54 Å (s.u. 0.001 Å) and C—O = 1.43 Å (s.u. 0.001 Å). The O8, O13, C31, C63, C71 and C72 atoms were refined isotropically to avoid non-positive definite or a large max/min ratio (more than 4) of the ADP.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
[CoBr(C32H38N2O4)(H2O)]·C4H8O | Dx = 1.374 Mg m−3 |
Mr = 743.62 | Mo Kα radiation, λ = 0.71073 Å |
Monoclinic, P21 | Cell parameters from 25 reflections |
a = 13.667 (2) Å | θ = 14.6–15.0° |
b = 15.046 (2) Å | µ = 1.64 mm−1 |
c = 17.764 (2) Å | T = 297 K |
β = 100.32 (1)° | Plate-like, brown |
V = 3593.8 (8) Å3 | 0.5 × 0.3 × 0.1 mm |
Z = 4 |
Rigaku AFC-7R diffractometer | Rint = 0.046 |
θ–2θ scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: integration (Coppens et al., 1965) | h = 0→18 |
Tmin = 0.619, Tmax = 0.854 | k = −14→20 |
12278 measured reflections | l = −23→23 |
11744 independent reflections | 3 standard reflections every 150 reflections |
6371 reflections with I > 2σ(I) | intensity decay: 1.7% |
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0754P)2 + 8.5404P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.064 | (Δ/σ)max = 0.020 |
wR(F2) = 0.186 | Δρmax = 0.70 e Å−3 |
S = 1.04 | Δρmin = −0.60 e Å−3 |
11744 reflections | Absolute structure: Flack (1983), 3169 Friedel pairs |
749 parameters | Absolute structure parameter: 0.04 (2) |
H-atom parameters not refined |
[CoBr(C32H38N2O4)(H2O)]·C4H8O | V = 3593.8 (8) Å3 |
Mr = 743.62 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 13.667 (2) Å | µ = 1.64 mm−1 |
b = 15.046 (2) Å | T = 297 K |
c = 17.764 (2) Å | 0.5 × 0.3 × 0.1 mm |
β = 100.32 (1)° |
Rigaku AFC-7R diffractometer | 6371 reflections with I > 2σ(I) |
Absorption correction: integration (Coppens et al., 1965) | Rint = 0.046 |
Tmin = 0.619, Tmax = 0.854 | 3 standard reflections every 150 reflections |
12278 measured reflections | intensity decay: 1.7% |
11744 independent reflections |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters not refined |
wR(F2) = 0.186 | Δρmax = 0.70 e Å−3 |
S = 1.04 | Δρmin = −0.60 e Å−3 |
11744 reflections | Absolute structure: Flack (1983), 3169 Friedel pairs |
749 parameters | Absolute structure parameter: 0.04 (2) |
Refinement. Refinement was based on F2 against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F2, and conventional R-factor (R) was calculated on F, with F set to zero for negative F2. The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt). |
x | y | z | Uiso*/Ueq | ||
Br1 | −0.2501 (1) | −0.0759 (4) | 0.35152 (9) | 0.0559 (5) | |
Br2 | 0.2532 (1) | 0.0659 (4) | 1.1453 (1) | 0.0611 (5) | |
Co3 | −0.1284 (1) | −0.0816 (4) | 0.4626 (1) | 0.0315 (5) | |
Co4 | 0.1249 (2) | 0.0805 (4) | 1.0379 (1) | 0.0391 (6) | |
O5 | −0.0494 (8) | −0.1588 (7) | 0.4126 (6) | 0.046 (3) | |
O6 | −0.0614 (7) | 0.0148 (8) | 0.4258 (6) | 0.046 (3) | |
O7 | −0.0605 (7) | −0.4315 (7) | 0.3980 (5) | 0.048 (3) | |
O8 | −0.1230 (7) | 0.2839 (8) | 0.4355 (6) | 0.06076 (4)* | |
O9 | −0.0226 (6) | −0.0892 (7) | 0.5567 (5) | 0.035 (2) | |
O10 | 0.0522 (7) | 0.1580 (8) | 1.0910 (6) | 0.046 (3) | |
O11 | 0.0538 (7) | −0.0134 (8) | 1.0737 (6) | 0.049 (3) | |
O12 | 0.0655 (8) | 0.4345 (8) | 1.1021 (6) | 0.064 (3) | |
O13 | 0.1265 (8) | −0.2818 (9) | 1.0793 (6) | 0.07646 (4)* | |
O14 | 0.0175 (7) | 0.0901 (8) | 0.9459 (6) | 0.048 (3) | |
O15 | 0.1797 (9) | −0.1483 (7) | 1.3017 (7) | 0.12530 (5)* | |
O16 | −0.172 (2) | 0.079 (1) | 0.187 (2) | 0.3024 (2)* | |
N17 | −0.1942 (9) | −0.1749 (8) | 0.5001 (7) | 0.042 (3) | |
N18 | −0.2087 (7) | −0.0085 (8) | 0.5117 (6) | 0.026 (2) | |
N19 | 0.1957 (7) | 0.1737 (8) | 1.0019 (6) | 0.027 (3) | |
N20 | 0.1877 (8) | 0.0025 (9) | 0.9803 (6) | 0.038 (3) | |
C21 | −0.060 (1) | −0.241 (1) | 0.4002 (9) | 0.045 (4) | |
C22 | −0.125 (1) | −0.2943 (9) | 0.4315 (8) | 0.034 (3) | |
C23 | −0.1826 (9) | −0.2609 (10) | 0.4819 (8) | 0.030 (3) | |
C24 | −0.2464 (8) | −0.1488 (8) | 0.5626 (7) | 0.035 (3) | |
C25 | −0.2869 (8) | −0.0535 (8) | 0.5439 (6) | 0.042 (3) | |
C26 | −0.209 (1) | 0.078 (1) | 0.5058 (8) | 0.040 (4) | |
C27 | −0.1507 (10) | 0.1328 (9) | 0.4623 (8) | 0.034 (4) | |
C28 | −0.082 (1) | 0.100 (1) | 0.4244 (9) | 0.042 (4) | |
C29 | 0.0092 (9) | −0.2699 (10) | 0.3465 (7) | 0.040 (3) | |
C30 | −0.130 (1) | −0.393 (1) | 0.4188 (9) | 0.046 (4) | |
C31 | −0.205 (1) | −0.447 (1) | 0.4487 (9) | 0.06704 (6)* | |
C32 | −0.3253 (9) | −0.2157 (9) | 0.5820 (8) | 0.031 (3) | |
C33 | −0.317 (1) | −0.2502 (9) | 0.6535 (9) | 0.040 (4) | |
C34 | −0.387 (1) | −0.305 (1) | 0.6719 (8) | 0.044 (4) | |
C35 | −0.470 (1) | −0.3336 (10) | 0.6200 (9) | 0.040 (3) | |
C36 | −0.4737 (10) | −0.3063 (10) | 0.5453 (8) | 0.043 (4) | |
C37 | −0.407 (1) | −0.2471 (9) | 0.5214 (9) | 0.040 (4) | |
C38 | −0.236 (1) | −0.2179 (10) | 0.7188 (8) | 0.065 (4) | |
C39 | −0.5451 (9) | −0.3961 (10) | 0.6413 (8) | 0.058 (4) | |
C40 | −0.418 (1) | −0.224 (1) | 0.4381 (8) | 0.050 (4) | |
C41 | −0.3165 (9) | −0.0074 (9) | 0.6110 (8) | 0.033 (3) | |
C42 | −0.2487 (9) | 0.0247 (10) | 0.6758 (9) | 0.044 (4) | |
C43 | −0.286 (2) | 0.074 (1) | 0.7341 (9) | 0.071 (5) | |
C44 | −0.386 (1) | 0.087 (1) | 0.729 (1) | 0.064 (5) | |
C45 | −0.454 (1) | 0.051 (1) | 0.667 (1) | 0.067 (5) | |
C46 | −0.424 (1) | 0.0069 (10) | 0.6091 (10) | 0.056 (4) | |
C47 | −0.140 (1) | 0.012 (1) | 0.6864 (9) | 0.068 (5) | |
C48 | −0.426 (2) | 0.136 (2) | 0.793 (1) | 0.120 (9) | |
C49 | −0.4994 (10) | −0.029 (1) | 0.5451 (9) | 0.060 (4) | |
C50 | −0.169 (1) | 0.2297 (9) | 0.4663 (9) | 0.047 (4) | |
C51 | −0.249 (2) | 0.268 (1) | 0.506 (1) | 0.095 (7) | |
C52 | −0.016 (1) | 0.150 (1) | 0.3792 (9) | 0.054 (4) | |
C53 | 0.059 (1) | 0.2420 (9) | 1.0984 (8) | 0.036 (4) | |
C54 | 0.1234 (10) | 0.296 (1) | 1.0628 (8) | 0.038 (4) | |
C55 | 0.192 (1) | 0.255 (1) | 1.0212 (8) | 0.038 (4) | |
C56 | 0.2799 (8) | 0.1383 (9) | 0.9665 (7) | 0.039 (3) | |
C57 | 0.2342 (8) | 0.0564 (8) | 0.9218 (6) | 0.036 (2) | |
C58 | 0.196 (1) | −0.082 (1) | 0.9880 (8) | 0.039 (3) | |
C59 | 0.151 (1) | −0.135 (1) | 1.0361 (8) | 0.043 (4) | |
C60 | 0.075 (1) | −0.094 (1) | 1.0747 (8) | 0.040 (4) | |
C61 | −0.001 (1) | 0.2814 (10) | 1.1527 (10) | 0.054 (5) | |
C62 | 0.127 (1) | 0.3904 (10) | 1.0729 (8) | 0.039 (4) | |
C63 | 0.221 (1) | 0.443 (2) | 1.063 (1) | 0.10463 (9)* | |
C64 | 0.336 (1) | 0.2066 (10) | 0.9319 (9) | 0.039 (3) | |
C65 | 0.416 (1) | 0.245 (1) | 0.9747 (9) | 0.054 (4) | |
C66 | 0.477 (1) | 0.304 (1) | 0.942 (1) | 0.085 (7) | |
C67 | 0.454 (1) | 0.329 (1) | 0.867 (1) | 0.063 (5) | |
C68 | 0.374 (1) | 0.296 (1) | 0.823 (1) | 0.060 (5) | |
C69 | 0.310 (1) | 0.2330 (9) | 0.8506 (9) | 0.041 (4) | |
C70 | 0.451 (1) | 0.223 (1) | 1.061 (1) | 0.072 (5) | |
C71 | 0.521 (1) | 0.392 (1) | 0.833 (1) | 0.10372 (9)* | |
C72 | 0.215 (1) | 0.214 (1) | 0.8034 (9) | 0.06748 (6)* | |
C73 | 0.291 (1) | 0.000 (1) | 0.8707 (8) | 0.047 (4) | |
C74 | 0.3911 (9) | −0.0162 (10) | 0.8908 (7) | 0.036 (3) | |
C75 | 0.434 (1) | −0.069 (1) | 0.837 (1) | 0.068 (5) | |
C76 | 0.378 (2) | −0.104 (1) | 0.770 (1) | 0.082 (7) | |
C77 | 0.281 (1) | −0.083 (1) | 0.7587 (10) | 0.072 (5) | |
C78 | 0.238 (2) | −0.0341 (10) | 0.8081 (9) | 0.063 (5) | |
C79 | 0.458 (1) | 0.0117 (10) | 0.960 (1) | 0.074 (5) | |
C80 | 0.430 (2) | −0.157 (1) | 0.720 (1) | 0.109 (8) | |
C81 | 0.124 (1) | −0.0240 (10) | 0.7847 (8) | 0.057 (4) | |
C82 | 0.171 (1) | −0.229 (1) | 1.0400 (8) | 0.043 (4) | |
C83 | 0.248 (1) | −0.266 (1) | 1.0023 (10) | 0.066 (5) | |
C84 | 0.019 (1) | −0.150 (1) | 1.1274 (10) | 0.066 (5) | |
C85 | 0.2803 (10) | −0.152 (1) | 1.290 (1) | 0.13210 (9)* | |
C86 | 0.324 (1) | −0.068 (1) | 1.333 (1) | 0.12039 (8)* | |
C87 | 0.242 (1) | −0.012 (1) | 1.360 (1) | 0.1601 (1)* | |
C88 | 0.151 (1) | −0.0587 (7) | 1.3136 (10) | 0.09850 (7)* | |
C89 | −0.233 (2) | 0.137 (1) | 0.222 (1) | 0.1557 (1)* | |
C90 | −0.333 (2) | 0.103 (2) | 0.177 (1) | 0.1864 (1)* | |
C91 | −0.292 (1) | 0.034 (1) | 0.127 (1) | 0.12957 (8)* | |
C92 | −0.190 (2) | −0.009 (1) | 0.156 (2) | 0.3464 (3)* | |
H9A | 0.0342 | −0.0513 | 0.5642 | 0.0434* | |
H9B | −0.0299 | −0.1340 | 0.5934 | 0.0434* | |
H14A | −0.0123 | 0.0375 | 0.9228 | 0.0578* | |
H14B | −0.0058 | 0.1456 | 0.9221 | 0.0578* | |
H23 | −0.2168 | −0.3037 | 0.5069 | 0.0357* | |
H24 | −0.1968 | −0.1443 | 0.6075 | 0.0415* | |
H25 | −0.3443 | −0.0580 | 0.5047 | 0.0495* | |
H26 | −0.2513 | 0.1089 | 0.5335 | 0.0474* | |
H29A | 0.0009 | −0.3323 | 0.3368 | 0.0492* | |
H29B | −0.0076 | −0.2387 | 0.2995 | 0.0492* | |
H29C | 0.0758 | −0.2582 | 0.3690 | 0.0492* | |
H31A | −0.2539 | −0.4085 | 0.4629 | 0.0832* | |
H31B | −0.2350 | −0.4869 | 0.4107 | 0.0832* | |
H31C | −0.1730 | −0.4788 | 0.4925 | 0.0832* | |
H34 | −0.3778 | −0.3260 | 0.7233 | 0.0527* | |
H36 | −0.5257 | −0.3294 | 0.5071 | 0.0506* | |
H38A | −0.2008 | −0.2680 | 0.7430 | 0.0792* | |
H38B | −0.1911 | −0.1802 | 0.6991 | 0.0792* | |
H38C | −0.2660 | −0.1866 | 0.7549 | 0.0792* | |
H39A | −0.6097 | −0.3722 | 0.6280 | 0.0712* | |
H39B | −0.5422 | −0.4516 | 0.6150 | 0.0712* | |
H39C | −0.5306 | −0.4075 | 0.6951 | 0.0712* | |
H40A | −0.3686 | −0.1822 | 0.4315 | 0.0622* | |
H40B | −0.4143 | −0.2750 | 0.4092 | 0.0622* | |
H40C | −0.4825 | −0.1963 | 0.4226 | 0.0622* | |
H43 | −0.2415 | 0.0974 | 0.7763 | 0.0844* | |
H45 | −0.5226 | 0.0596 | 0.6659 | 0.0824* | |
H47A | −0.1177 | −0.0186 | 0.7330 | 0.0804* | |
H47B | −0.1245 | −0.0215 | 0.6449 | 0.0804* | |
H47C | −0.1085 | 0.0685 | 0.6880 | 0.0804* | |
H48A | −0.3754 | 0.1572 | 0.8300 | 0.1496* | |
H48B | −0.4678 | 0.1856 | 0.7709 | 0.1496* | |
H48C | −0.4690 | 0.0970 | 0.8153 | 0.1496* | |
H49A | −0.5378 | 0.0190 | 0.5206 | 0.0751* | |
H49B | −0.4668 | −0.0585 | 0.5096 | 0.0751* | |
H49C | −0.5418 | −0.0694 | 0.5650 | 0.0751* | |
H51A | −0.2201 | 0.3081 | 0.5447 | 0.1114* | |
H51B | −0.2967 | 0.2994 | 0.4693 | 0.1114* | |
H51C | −0.2820 | 0.2217 | 0.5276 | 0.1114* | |
H52A | 0.0522 | 0.1409 | 0.4029 | 0.0631* | |
H52B | −0.0253 | 0.1270 | 0.3286 | 0.0631* | |
H52C | −0.0310 | 0.2107 | 0.3786 | 0.0631* | |
H55 | 0.2412 | 0.2927 | 1.0066 | 0.0452* | |
H56 | 0.3262 | 0.1145 | 1.0081 | 0.0465* | |
H57 | 0.1788 | 0.0790 | 0.8875 | 0.0429* | |
H58 | 0.2371 | −0.1112 | 0.9580 | 0.0473* | |
H61A | 0.0067 | 0.3435 | 1.1544 | 0.0654* | |
H61B | −0.0703 | 0.2675 | 1.1346 | 0.0654* | |
H61C | 0.0185 | 0.2562 | 1.2018 | 0.0654* | |
H63A | 0.2632 | 0.4068 | 1.0400 | 0.1219* | |
H63B | 0.2004 | 0.4933 | 1.0299 | 0.1219* | |
H63C | 0.2533 | 0.4642 | 1.1107 | 0.1219* | |
H66 | 0.5344 | 0.3282 | 0.9733 | 0.1004* | |
H68 | 0.3600 | 0.3138 | 0.7715 | 0.0726* | |
H70A | 0.4042 | 0.1816 | 1.0763 | 0.0902* | |
H70B | 0.5142 | 0.1956 | 1.0679 | 0.0902* | |
H70C | 0.4525 | 0.2748 | 1.0901 | 0.0902* | |
H71A | 0.5751 | 0.4081 | 0.8731 | 0.1249* | |
H71B | 0.5480 | 0.3606 | 0.7946 | 0.1249* | |
H71C | 0.4859 | 0.4414 | 0.8132 | 0.1249* | |
H72A | 0.1770 | 0.2661 | 0.7948 | 0.0817* | |
H72B | 0.2254 | 0.1895 | 0.7559 | 0.0817* | |
H72C | 0.1811 | 0.1710 | 0.8289 | 0.0817* | |
H75 | 0.5038 | −0.0793 | 0.8481 | 0.0800* | |
H77 | 0.2396 | −0.1047 | 0.7133 | 0.0866* | |
H79A | 0.4862 | −0.0392 | 0.9883 | 0.0867* | |
H79B | 0.5101 | 0.0471 | 0.9474 | 0.0867* | |
H79C | 0.4222 | 0.0453 | 0.9918 | 0.0867* | |
H80A | 0.4572 | −0.2083 | 0.7462 | 0.1295* | |
H80B | 0.3809 | −0.1764 | 0.6760 | 0.1295* | |
H80C | 0.4782 | −0.1232 | 0.7024 | 0.1295* | |
H81A | 0.0988 | 0.0107 | 0.8217 | 0.0680* | |
H81B | 0.1084 | 0.0044 | 0.7362 | 0.0680* | |
H81C | 0.0932 | −0.0811 | 0.7815 | 0.0680* | |
H83A | 0.2985 | −0.2915 | 1.0392 | 0.0803* | |
H83B | 0.2193 | −0.3101 | 0.9668 | 0.0803* | |
H83C | 0.2751 | −0.2199 | 0.9757 | 0.0803* | |
H84A | 0.0369 | −0.1289 | 1.1787 | 0.0821* | |
H84B | −0.0494 | −0.1460 | 1.1107 | 0.0821* | |
H84C | 0.0402 | −0.2109 | 1.1263 | 0.0821* | |
H85A | 0.3137 | −0.2036 | 1.3126 | 0.1543* | |
H85B | 0.2851 | −0.1493 | 1.2376 | 0.1543* | |
H86A | 0.3721 | −0.0838 | 1.3759 | 0.1431* | |
H86B | 0.3546 | −0.0319 | 1.2992 | 0.1431* | |
H87A | 0.2442 | −0.0173 | 1.4137 | 0.1893* | |
H87B | 0.2451 | 0.0490 | 1.3470 | 0.1893* | |
H88A | 0.1306 | −0.0297 | 1.2658 | 0.1172* | |
H88B | 0.0972 | −0.0584 | 1.3412 | 0.1172* | |
H89A | −0.2260 | 0.1277 | 0.2754 | 0.1870* | |
H89B | −0.2221 | 0.1979 | 0.2121 | 0.1870* | |
H90A | −0.3725 | 0.0754 | 0.2100 | 0.2207* | |
H90B | −0.3708 | 0.1481 | 0.1483 | 0.2207* | |
H91A | −0.3394 | −0.0118 | 0.1159 | 0.1541* | |
H91B | −0.2862 | 0.0642 | 0.0801 | 0.1541* | |
H92A | −0.1530 | −0.0273 | 0.1191 | 0.4292* | |
H92B | −0.1903 | −0.0553 | 0.1931 | 0.4292* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.071 (1) | 0.0512 (10) | 0.045 (1) | −0.0017 (10) | 0.0101 (9) | 0.0009 (9) |
Br2 | 0.086 (1) | 0.052 (1) | 0.043 (1) | 0.0007 (9) | 0.0052 (9) | 0.0064 (8) |
Co3 | 0.037 (1) | 0.0207 (9) | 0.040 (1) | −0.0028 (9) | 0.0156 (9) | −0.0014 (9) |
Co4 | 0.052 (1) | 0.029 (1) | 0.039 (1) | −0.0005 (10) | 0.016 (1) | 0.0021 (9) |
O5 | 0.069 (7) | 0.009 (5) | 0.067 (7) | −0.002 (4) | 0.033 (6) | −0.002 (4) |
O6 | 0.054 (6) | 0.039 (6) | 0.052 (7) | −0.002 (5) | 0.030 (5) | 0.009 (5) |
O7 | 0.062 (7) | 0.032 (6) | 0.054 (7) | 0.006 (5) | 0.024 (5) | −0.012 (5) |
O9 | 0.039 (5) | 0.024 (5) | 0.048 (6) | −0.002 (4) | 0.020 (4) | 0.001 (4) |
O10 | 0.039 (6) | 0.060 (7) | 0.045 (7) | 0.003 (5) | 0.022 (5) | 0.004 (5) |
O11 | 0.057 (6) | 0.030 (6) | 0.066 (7) | −0.004 (5) | 0.024 (5) | −0.009 (5) |
O12 | 0.083 (8) | 0.037 (6) | 0.075 (8) | 0.020 (6) | 0.023 (7) | 0.019 (6) |
O14 | 0.036 (5) | 0.043 (6) | 0.062 (7) | −0.006 (5) | 0.000 (5) | 0.007 (5) |
N17 | 0.055 (8) | 0.029 (7) | 0.051 (8) | 0.004 (6) | 0.037 (7) | 0.007 (6) |
N18 | 0.024 (5) | 0.016 (5) | 0.039 (6) | 0.000 (4) | 0.011 (4) | 0.001 (4) |
N19 | 0.030 (6) | 0.024 (6) | 0.026 (6) | −0.001 (5) | −0.001 (5) | 0.002 (5) |
N20 | 0.040 (6) | 0.033 (6) | 0.044 (7) | −0.012 (5) | 0.010 (5) | 0.000 (5) |
C21 | 0.037 (8) | 0.048 (10) | 0.051 (10) | 0.023 (7) | 0.014 (7) | 0.024 (8) |
C22 | 0.047 (9) | 0.012 (6) | 0.042 (8) | −0.003 (6) | 0.008 (7) | 0.002 (6) |
C23 | 0.020 (6) | 0.029 (8) | 0.042 (9) | 0.005 (5) | 0.009 (6) | 0.007 (6) |
C24 | 0.038 (7) | 0.012 (5) | 0.058 (8) | 0.000 (5) | 0.016 (6) | 0.001 (5) |
C25 | 0.050 (7) | 0.033 (6) | 0.048 (7) | 0.010 (5) | 0.023 (6) | 0.011 (5) |
C26 | 0.045 (8) | 0.039 (9) | 0.036 (8) | −0.010 (7) | 0.007 (6) | −0.014 (7) |
C27 | 0.029 (8) | 0.023 (7) | 0.05 (1) | 0.000 (6) | 0.007 (7) | −0.004 (7) |
C28 | 0.06 (1) | 0.020 (7) | 0.039 (9) | −0.016 (7) | −0.003 (8) | 0.006 (6) |
C29 | 0.039 (7) | 0.050 (8) | 0.029 (7) | 0.011 (6) | −0.001 (6) | −0.001 (6) |
C30 | 0.06 (1) | 0.044 (9) | 0.032 (8) | −0.006 (8) | 0.011 (7) | −0.004 (7) |
C32 | 0.025 (6) | 0.017 (6) | 0.054 (9) | 0.001 (5) | 0.019 (6) | −0.003 (6) |
C33 | 0.042 (8) | 0.020 (6) | 0.055 (9) | −0.001 (6) | 0.001 (7) | −0.003 (6) |
C34 | 0.059 (9) | 0.039 (8) | 0.038 (8) | 0.004 (7) | 0.023 (8) | 0.008 (7) |
C35 | 0.046 (8) | 0.034 (7) | 0.045 (8) | 0.000 (6) | 0.018 (7) | −0.003 (6) |
C36 | 0.033 (8) | 0.030 (7) | 0.059 (9) | 0.001 (6) | −0.007 (6) | 0.005 (6) |
C37 | 0.049 (8) | 0.011 (6) | 0.06 (1) | −0.008 (6) | 0.018 (8) | −0.003 (6) |
C38 | 0.08 (1) | 0.059 (8) | 0.046 (8) | −0.012 (7) | −0.010 (7) | 0.010 (7) |
C39 | 0.040 (7) | 0.061 (8) | 0.078 (10) | −0.026 (6) | 0.024 (7) | 0.012 (7) |
C40 | 0.046 (8) | 0.056 (8) | 0.044 (8) | −0.001 (6) | −0.008 (6) | 0.005 (7) |
C41 | 0.041 (7) | 0.021 (6) | 0.038 (7) | −0.006 (5) | 0.012 (6) | 0.004 (5) |
C42 | 0.037 (7) | 0.038 (8) | 0.07 (1) | 0.003 (6) | 0.036 (7) | 0.001 (7) |
C43 | 0.13 (2) | 0.032 (9) | 0.050 (10) | −0.001 (10) | 0.03 (1) | −0.004 (7) |
C44 | 0.08 (1) | 0.039 (8) | 0.08 (1) | −0.001 (8) | 0.05 (1) | −0.016 (8) |
C45 | 0.062 (10) | 0.059 (10) | 0.09 (1) | 0.004 (8) | 0.037 (9) | −0.016 (9) |
C46 | 0.055 (9) | 0.031 (7) | 0.09 (1) | 0.020 (6) | 0.036 (8) | −0.002 (7) |
C47 | 0.08 (1) | 0.060 (9) | 0.07 (1) | −0.010 (8) | 0.032 (8) | −0.029 (8) |
C48 | 0.13 (2) | 0.13 (2) | 0.12 (2) | −0.02 (1) | 0.07 (1) | −0.07 (2) |
C49 | 0.044 (8) | 0.065 (9) | 0.074 (10) | −0.002 (7) | 0.014 (7) | 0.012 (7) |
C50 | 0.07 (1) | 0.016 (7) | 0.051 (10) | −0.013 (7) | −0.001 (8) | 0.008 (6) |
C51 | 0.11 (2) | 0.018 (8) | 0.16 (2) | 0.009 (9) | 0.05 (1) | −0.016 (10) |
C52 | 0.07 (1) | 0.051 (10) | 0.047 (9) | 0.010 (8) | 0.021 (8) | 0.014 (8) |
C53 | 0.044 (9) | 0.019 (7) | 0.046 (9) | −0.004 (6) | 0.010 (7) | −0.015 (6) |
C54 | 0.032 (8) | 0.040 (9) | 0.042 (9) | 0.006 (6) | 0.011 (7) | 0.008 (7) |
C55 | 0.050 (9) | 0.037 (9) | 0.031 (8) | −0.003 (7) | 0.014 (7) | 0.000 (7) |
C56 | 0.032 (7) | 0.040 (7) | 0.048 (8) | 0.008 (5) | 0.015 (6) | 0.005 (6) |
C57 | 0.046 (6) | 0.032 (5) | 0.036 (6) | 0.004 (5) | 0.020 (5) | 0.009 (5) |
C58 | 0.055 (8) | 0.021 (7) | 0.043 (8) | 0.004 (7) | 0.019 (7) | 0.006 (7) |
C59 | 0.042 (9) | 0.044 (10) | 0.04 (1) | −0.011 (8) | 0.003 (8) | 0.010 (8) |
C60 | 0.042 (8) | 0.046 (10) | 0.029 (8) | 0.002 (7) | 0.000 (7) | 0.006 (7) |
C61 | 0.057 (8) | 0.019 (6) | 0.10 (1) | −0.005 (6) | 0.057 (9) | −0.001 (6) |
C62 | 0.047 (9) | 0.031 (8) | 0.038 (8) | 0.018 (7) | 0.007 (7) | −0.001 (6) |
C64 | 0.049 (8) | 0.020 (6) | 0.049 (8) | 0.002 (6) | 0.013 (7) | 0.007 (6) |
C65 | 0.06 (1) | 0.06 (1) | 0.05 (1) | 0.004 (9) | 0.010 (9) | 0.006 (8) |
C66 | 0.029 (9) | 0.06 (1) | 0.16 (2) | −0.010 (9) | 0.02 (1) | −0.05 (1) |
C67 | 0.06 (1) | 0.044 (9) | 0.09 (1) | −0.007 (8) | 0.03 (1) | 0.020 (9) |
C68 | 0.07 (1) | 0.049 (10) | 0.07 (1) | 0.005 (8) | 0.029 (9) | 0.021 (9) |
C69 | 0.047 (8) | 0.022 (6) | 0.055 (9) | −0.001 (6) | 0.014 (7) | 0.017 (6) |
C70 | 0.07 (1) | 0.07 (1) | 0.08 (1) | −0.019 (8) | −0.004 (8) | −0.018 (9) |
C73 | 0.08 (1) | 0.029 (7) | 0.038 (8) | 0.009 (7) | 0.021 (7) | 0.001 (6) |
C74 | 0.038 (8) | 0.039 (7) | 0.033 (7) | 0.001 (6) | 0.011 (6) | −0.003 (5) |
C75 | 0.047 (8) | 0.043 (8) | 0.12 (1) | 0.022 (7) | 0.029 (9) | 0.034 (10) |
C76 | 0.13 (2) | 0.042 (9) | 0.09 (2) | 0.022 (10) | 0.06 (1) | −0.001 (9) |
C77 | 0.07 (1) | 0.09 (1) | 0.07 (1) | 0.01 (1) | 0.040 (10) | 0.00 (1) |
C78 | 0.14 (2) | 0.021 (7) | 0.040 (8) | 0.002 (8) | 0.041 (9) | 0.003 (6) |
C79 | 0.08 (1) | 0.034 (7) | 0.11 (1) | 0.013 (7) | 0.03 (1) | −0.003 (8) |
C80 | 0.19 (2) | 0.06 (1) | 0.10 (2) | 0.02 (1) | 0.09 (2) | −0.010 (10) |
C81 | 0.079 (10) | 0.041 (8) | 0.056 (9) | −0.018 (7) | 0.026 (8) | 0.015 (7) |
C82 | 0.040 (9) | 0.07 (1) | 0.018 (7) | −0.014 (8) | −0.003 (6) | 0.001 (7) |
C83 | 0.09 (1) | 0.049 (10) | 0.063 (10) | 0.005 (9) | 0.015 (9) | 0.021 (8) |
C84 | 0.09 (1) | 0.06 (1) | 0.06 (1) | −0.045 (9) | 0.029 (10) | −0.002 (9) |
Br1—Co3 | 2.345 (2) | C50—C51 | 1.52 (3) |
Br2—Co4 | 2.359 (3) | C51—H51A | 0.944 |
Co3—O5 | 1.91 (1) | C51—H51B | 0.964 |
Co3—O6 | 1.89 (1) | C51—H51C | 0.942 |
Co3—O9 | 2.007 (8) | C52—H52A | 0.961 |
Co3—N17 | 1.85 (1) | C52—H52B | 0.948 |
Co3—N18 | 1.88 (1) | C52—H52C | 0.941 |
Co4—O10 | 1.89 (1) | C53—C54 | 1.43 (2) |
Co4—O11 | 1.89 (1) | C53—C61 | 1.50 (2) |
Co4—O14 | 1.997 (9) | C54—C55 | 1.43 (2) |
Co4—N19 | 1.88 (1) | C54—C62 | 1.43 (2) |
Co4—N20 | 1.87 (1) | C55—H55 | 0.948 |
O5—C21 | 1.26 (2) | C56—C57 | 1.54 (2) |
O6—C28 | 1.31 (2) | C56—C64 | 1.49 (2) |
O7—C30 | 1.22 (2) | C56—H56 | 0.952 |
O8—C50 | 1.22 (2) | C57—C73 | 1.55 (2) |
O9—H9A | 0.953 | C57—H57 | 0.946 |
O9—H9B | 0.956 | C58—C59 | 1.39 (2) |
O10—C53 | 1.27 (2) | C58—H58 | 0.948 |
O11—C60 | 1.25 (2) | C59—C60 | 1.48 (2) |
O12—C62 | 1.25 (2) | C59—C82 | 1.43 (2) |
O13—C82 | 1.29 (2) | C60—C84 | 1.55 (2) |
O14—H14A | 0.950 | C61—H61A | 0.940 |
O14—H14B | 0.964 | C61—H61B | 0.964 |
O15—C85 | 1.43 (2) | C61—H61C | 0.945 |
O15—C88 | 1.43 (2) | C62—C63 | 1.55 (3) |
O16—C89 | 1.43 (4) | C63—H63A | 0.940 |
O16—C92 | 1.43 (3) | C63—H63B | 0.962 |
N17—C23 | 1.35 (2) | C63—H63C | 0.944 |
N17—C24 | 1.48 (2) | C64—C65 | 1.34 (2) |
N18—C25 | 1.46 (2) | C64—C69 | 1.48 (2) |
N18—C26 | 1.30 (2) | C65—C66 | 1.41 (3) |
N19—C55 | 1.28 (2) | C65—C70 | 1.55 (2) |
N19—C56 | 1.50 (2) | C66—C67 | 1.38 (3) |
N20—C57 | 1.54 (2) | C66—H66 | 0.946 |
N20—C58 | 1.29 (2) | C67—C68 | 1.32 (2) |
C21—C22 | 1.39 (2) | C67—C71 | 1.50 (3) |
C21—C29 | 1.52 (2) | C68—C69 | 1.43 (2) |
C22—C23 | 1.39 (2) | C68—H68 | 0.946 |
C22—C30 | 1.50 (2) | C69—C72 | 1.45 (2) |
C23—H23 | 0.951 | C70—H70A | 0.959 |
C24—C25 | 1.55 (2) | C70—H70B | 0.947 |
C24—C32 | 1.56 (2) | C70—H70C | 0.944 |
C24—H24 | 0.952 | C71—H71A | 0.957 |
C25—C41 | 1.50 (2) | C71—H71B | 0.961 |
C25—H25 | 0.953 | C71—H71C | 0.926 |
C26—C27 | 1.46 (2) | C72—H72A | 0.938 |
C26—H26 | 0.947 | C72—H72B | 0.954 |
C27—C28 | 1.34 (2) | C72—H72C | 0.953 |
C27—C50 | 1.48 (2) | C73—C74 | 1.37 (2) |
C28—C52 | 1.51 (2) | C73—C78 | 1.32 (2) |
C29—H29A | 0.957 | C74—C75 | 1.44 (2) |
C29—H29B | 0.951 | C74—C79 | 1.46 (2) |
C29—H29C | 0.942 | C75—C76 | 1.41 (3) |
C30—C31 | 1.48 (2) | C75—H75 | 0.955 |
C31—H31A | 0.949 | C76—C77 | 1.34 (3) |
C31—H31B | 0.944 | C76—C80 | 1.47 (3) |
C31—H31C | 0.952 | C77—C78 | 1.36 (3) |
C32—C33 | 1.36 (2) | C77—H77 | 0.958 |
C32—C37 | 1.48 (2) | C78—C81 | 1.54 (3) |
C33—C34 | 1.35 (2) | C79—H79A | 0.958 |
C33—C38 | 1.53 (2) | C79—H79B | 0.952 |
C34—C35 | 1.40 (2) | C79—H79C | 0.950 |
C34—H34 | 0.951 | C80—H80A | 0.938 |
C35—C36 | 1.38 (2) | C80—H80B | 0.977 |
C35—C39 | 1.50 (2) | C80—H80C | 0.927 |
C36—C37 | 1.39 (2) | C81—H81A | 0.952 |
C36—H36 | 0.955 | C81—H81B | 0.951 |
C37—C40 | 1.50 (2) | C81—H81C | 0.953 |
C38—H38A | 0.953 | C82—C83 | 1.46 (2) |
C38—H38B | 0.949 | C83—H83A | 0.945 |
C38—H38C | 0.946 | C83—H83B | 0.948 |
C39—H39A | 0.942 | C83—H83C | 0.954 |
C39—H39B | 0.961 | C84—H84A | 0.953 |
C39—H39C | 0.955 | C84—H84B | 0.936 |
C40—H40A | 0.946 | C84—H84C | 0.962 |
C40—H40B | 0.931 | C85—C86 | 1.54 (2) |
C40—H40C | 0.967 | C85—H85A | 0.954 |
C41—C42 | 1.43 (2) | C85—H85B | 0.943 |
C41—C46 | 1.48 (2) | C86—C87 | 1.54 (3) |
C42—C43 | 1.44 (2) | C86—H86A | 0.952 |
C42—C47 | 1.48 (2) | C86—H86B | 0.954 |
C43—C44 | 1.37 (3) | C87—C88 | 1.54 (2) |
C43—H43 | 0.940 | C87—H87A | 0.951 |
C44—C45 | 1.41 (2) | C87—H87B | 0.948 |
C44—C48 | 1.54 (3) | C88—H88A | 0.950 |
C45—C46 | 1.35 (3) | C88—H88B | 0.954 |
C45—H45 | 0.948 | C89—C90 | 1.54 (3) |
C46—C49 | 1.49 (2) | C89—H89A | 0.952 |
C47—H47A | 0.949 | C89—H89B | 0.953 |
C47—H47B | 0.949 | C90—C91 | 1.54 (3) |
C47—H47C | 0.948 | C90—H90A | 0.960 |
C48—H48A | 0.911 | C90—H90B | 0.939 |
C48—H48B | 0.979 | C91—C92 | 1.54 (3) |
C48—H48C | 0.968 | C91—H91A | 0.946 |
C49—H49A | 0.945 | C91—H91B | 0.955 |
C49—H49B | 0.948 | C92—H92A | 0.939 |
C49—H49C | 0.955 | C92—H92B | 0.961 |
Br1—Co3—O5 | 90.3 (3) | H52A—C52—H52B | 108 |
Br1—Co3—O6 | 89.7 (3) | H52A—C52—H52C | 109 |
Br1—Co3—O9 | 178.6 (4) | H52B—C52—H52C | 110 |
Br1—Co3—N17 | 90.7 (4) | O10—C53—C54 | 124 (1) |
Br1—Co3—N18 | 89.1 (3) | O10—C53—C61 | 115 (1) |
O5—Co3—O6 | 87.5 (5) | C54—C53—C61 | 120 (1) |
O5—Co3—O9 | 88.3 (4) | C53—C54—C55 | 119 (1) |
O5—Co3—N17 | 93.3 (6) | C53—C54—C62 | 121 (1) |
O5—Co3—N18 | 178.3 (5) | C55—C54—C62 | 118 (1) |
O6—Co3—O9 | 90.6 (4) | N19—C55—C54 | 127 (1) |
O6—Co3—N17 | 179.1 (6) | N19—C55—H55 | 115 |
O6—Co3—N18 | 94.1 (5) | C54—C55—H55 | 116 |
O9—Co3—N17 | 89.0 (5) | N19—C56—C57 | 103.3 (9) |
O9—Co3—N18 | 92.3 (4) | N19—C56—C64 | 114 (1) |
N17—Co3—N18 | 85.1 (5) | N19—C56—H56 | 105 |
Br2—Co4—O10 | 92.0 (3) | C57—C56—C64 | 122 (1) |
Br2—Co4—O11 | 90.6 (3) | C57—C56—H56 | 104 |
Br2—Co4—O14 | 178.6 (4) | C64—C56—H56 | 105 |
Br2—Co4—N19 | 89.5 (3) | N20—C57—C56 | 104.5 (9) |
Br2—Co4—N20 | 92.1 (3) | N20—C57—C73 | 114 (1) |
O10—Co4—O11 | 86.9 (5) | N20—C57—H57 | 104.2 |
O10—Co4—O14 | 89.3 (4) | C56—C57—C73 | 122 (1) |
O10—Co4—N19 | 93.4 (6) | C56—C57—H57 | 104 |
O10—Co4—N20 | 175.6 (4) | C73—C57—H57 | 104.4 |
O11—Co4—O14 | 89.0 (4) | N20—C58—C59 | 126 (1) |
O11—Co4—N19 | 179.7 (5) | N20—C58—H58 | 116 |
O11—Co4—N20 | 91.6 (6) | C59—C58—H58 | 116 |
O14—Co4—N19 | 90.9 (5) | C58—C59—C60 | 117 (1) |
O14—Co4—N20 | 86.5 (5) | C58—C59—C82 | 119 (1) |
N19—Co4—N20 | 88.1 (5) | C60—C59—C82 | 122 (1) |
Co3—O5—C21 | 128 (1) | O11—C60—C59 | 125 (1) |
Co3—O6—C28 | 129 (1) | O11—C60—C84 | 113 (1) |
Co3—O9—H9A | 122.0 | C59—C60—C84 | 120 (1) |
Co3—O9—H9B | 117.4 | C53—C61—H61A | 109 |
H9A—O9—H9B | 120.5 | C53—C61—H61B | 108 |
Co4—O10—C53 | 129 (1) | C53—C61—H61C | 109 |
Co4—O11—C60 | 127 (1) | H61A—C61—H61B | 109 |
Co4—O14—H14A | 119.2 | H61A—C61—H61C | 110 |
Co4—O14—H14B | 123.9 | H61B—C61—H61C | 108 |
H14A—O14—H14B | 116.8 | O12—C62—C54 | 124 (1) |
C85—O15—C88 | 110 (1) | O12—C62—C63 | 114 (1) |
C89—O16—C92 | 130 (2) | C54—C62—C63 | 120 (1) |
Co3—N17—C23 | 123 (1) | C62—C63—H63A | 109 |
Co3—N17—C24 | 113.6 (9) | C62—C63—H63B | 108 |
C23—N17—C24 | 121 (1) | C62—C63—H63C | 109 |
Co3—N18—C25 | 116.1 (8) | H63A—C63—H63B | 109 |
Co3—N18—C26 | 122 (1) | H63A—C63—H63C | 110 |
C25—N18—C26 | 119 (1) | H63B—C63—H63C | 108 |
Co4—N19—C55 | 125 (1) | C56—C64—C65 | 119 (1) |
Co4—N19—C56 | 110.9 (8) | C56—C64—C69 | 122 (1) |
C55—N19—C56 | 121 (1) | C65—C64—C69 | 117 (1) |
Co4—N20—C57 | 109.0 (9) | C64—C65—C66 | 121 (1) |
Co4—N20—C58 | 127 (1) | C64—C65—C70 | 122 (1) |
C57—N20—C58 | 123 (1) | C66—C65—C70 | 116 (1) |
O5—C21—C22 | 124 (1) | C65—C66—C67 | 121 (1) |
O5—C21—C29 | 109 (1) | C65—C66—H66 | 119 |
C22—C21—C29 | 126 (1) | C67—C66—H66 | 118 |
C21—C22—C23 | 121 (1) | C66—C67—C68 | 118 (1) |
C21—C22—C30 | 121 (1) | C66—C67—C71 | 120 (1) |
C23—C22—C30 | 116 (1) | C68—C67—C71 | 120 (1) |
N17—C23—C22 | 127 (1) | C67—C68—C69 | 123 (1) |
N17—C23—H23 | 116 | C67—C68—H68 | 117 |
C22—C23—H23 | 116 | C69—C68—H68 | 118 |
N17—C24—C25 | 106.6 (10) | C64—C69—C68 | 116 (1) |
N17—C24—C32 | 116 (1) | C64—C69—C72 | 123 (1) |
N17—C24—H24 | 106 | C68—C69—C72 | 118 (1) |
C25—C24—C32 | 114.2 (10) | C65—C70—H70A | 108 |
C25—C24—H24 | 106 | C65—C70—H70B | 109 |
C32—C24—H24 | 106 | C65—C70—H70C | 109 |
N18—C25—C24 | 104.7 (9) | H70A—C70—H70B | 108 |
N18—C25—C41 | 114.7 (10) | H70A—C70—H70C | 109 |
N18—C25—H25 | 108 | H70B—C70—H70C | 110 |
C24—C25—C41 | 113.2 (10) | C67—C71—H71A | 108 |
C24—C25—H25 | 107.8 | C67—C71—H71B | 108 |
C41—C25—H25 | 108 | C67—C71—H71C | 110 |
N18—C26—C27 | 127 (1) | H71A—C71—H71B | 108 |
N18—C26—H26 | 116 | H71A—C71—H71C | 111 |
C27—C26—H26 | 115 | H71B—C71—H71C | 110 |
C26—C27—C28 | 123 (1) | C69—C72—H72A | 109 |
C26—C27—C50 | 114 (1) | C69—C72—H72B | 108 |
C28—C27—C50 | 121 (1) | C69—C72—H72C | 108 |
O6—C28—C27 | 121 (1) | H72A—C72—H72B | 110 |
O6—C28—C52 | 110 (1) | H72A—C72—H72C | 110 |
C27—C28—C52 | 128 (1) | H72B—C72—H72C | 108 |
C21—C29—H29A | 109 | C57—C73—C74 | 121 (1) |
C21—C29—H29B | 109 | C57—C73—C78 | 116 (1) |
C21—C29—H29C | 109 | C74—C73—C78 | 121 (1) |
H29A—C29—H29B | 108 | C73—C74—C75 | 115 (1) |
H29A—C29—H29C | 109 | C73—C74—C79 | 127 (1) |
H29B—C29—H29C | 110 | C75—C74—C79 | 116 (1) |
O7—C30—C22 | 120 (1) | C74—C75—C76 | 123 (1) |
O7—C30—C31 | 118 (1) | C74—C75—H75 | 117 |
C22—C30—C31 | 120 (1) | C76—C75—H75 | 118 |
C30—C31—H31A | 109 | C75—C76—C77 | 113 (1) |
C30—C31—H31B | 109 | C75—C76—C80 | 118 (1) |
C30—C31—H31C | 108 | C77—C76—C80 | 127 (1) |
H31A—C31—H31B | 110 | C76—C77—C78 | 124 (1) |
H31A—C31—H31C | 109 | C76—C77—H77 | 117 |
H31B—C31—H31C | 109 | C78—C77—H77 | 117 |
C24—C32—C33 | 120 (1) | C73—C78—C77 | 120 (1) |
C24—C32—C37 | 120 (1) | C73—C78—C81 | 124 (1) |
C33—C32—C37 | 119 (1) | C77—C78—C81 | 114 (1) |
C32—C33—C34 | 120 (1) | C74—C79—H79A | 110 |
C32—C33—C38 | 121 (1) | C74—C79—H79B | 109 |
C34—C33—C38 | 117 (1) | C74—C79—H79C | 110 |
C33—C34—C35 | 123 (1) | H79A—C79—H79B | 108 |
C33—C34—H34 | 117 | H79A—C79—H79C | 108 |
C35—C34—H34 | 118 | H79B—C79—H79C | 109 |
C34—C35—C36 | 115 (1) | C76—C80—H80A | 109 |
C34—C35—C39 | 122 (1) | C76—C80—H80B | 107 |
C36—C35—C39 | 121 (1) | C76—C80—H80C | 110 |
C35—C36—C37 | 124 (1) | H80A—C80—H80B | 108 |
C35—C36—H36 | 118 | H80A—C80—H80C | 112 |
C37—C36—H36 | 117 | H80B—C80—H80C | 109 |
C32—C37—C36 | 115 (1) | C78—C81—H81A | 109 |
C32—C37—C40 | 124 (1) | C78—C81—H81B | 109 |
C36—C37—C40 | 119 (1) | C78—C81—H81C | 109 |
C33—C38—H38A | 109 | H81A—C81—H81B | 109 |
C33—C38—H38B | 109 | H81A—C81—H81C | 109 |
C33—C38—H38C | 109 | H81B—C81—H81C | 109 |
H38A—C38—H38B | 109 | O13—C82—C59 | 122 (1) |
H38A—C38—H38C | 109 | O13—C82—C83 | 117 (1) |
H38B—C38—H38C | 109 | C59—C82—C83 | 120 (1) |
C35—C39—H39A | 110 | C82—C83—H83A | 109 |
C35—C39—H39B | 109 | C82—C83—H83B | 109 |
C35—C39—H39C | 109 | C82—C83—H83C | 108 |
H39A—C39—H39B | 109 | H83A—C83—H83B | 110 |
H39A—C39—H39C | 109 | H83A—C83—H83C | 109 |
H39B—C39—H39C | 108 | H83B—C83—H83C | 109 |
C37—C40—H40A | 109 | C60—C84—H84A | 109 |
C37—C40—H40B | 110 | C60—C84—H84B | 110 |
C37—C40—H40C | 107 | C60—C84—H84C | 108 |
H40A—C40—H40B | 111 | H84A—C84—H84B | 110 |
H40A—C40—H40C | 108 | H84A—C84—H84C | 108 |
H40B—C40—H40C | 109 | H84B—C84—H84C | 109 |
C25—C41—C42 | 124 (1) | O15—C85—C86 | 101 (1) |
C25—C41—C46 | 117 (1) | O15—C85—H85A | 111 |
C42—C41—C46 | 117 (1) | O15—C85—H85B | 112 |
C41—C42—C43 | 119 (1) | C86—C85—H85A | 110 |
C41—C42—C47 | 123 (1) | C86—C85—H85B | 111 |
C43—C42—C47 | 116 (1) | H85A—C85—H85B | 109 |
C42—C43—C44 | 120 (1) | C85—C86—C87 | 111 (1) |
C42—C43—H43 | 120 | C85—C86—H86A | 109 |
C44—C43—H43 | 119 | C85—C86—H86B | 109 |
C43—C44—C45 | 120 (1) | C87—C86—H86A | 108 |
C43—C44—C48 | 119 (1) | C87—C86—H86B | 108 |
C45—C44—C48 | 119 (1) | H86A—C86—H86B | 108 |
C44—C45—C46 | 122 (1) | C86—C87—C88 | 98 (1) |
C44—C45—H45 | 118 | C86—C87—H87A | 112 |
C46—C45—H45 | 118 | C86—C87—H87B | 112 |
C41—C46—C45 | 119 (1) | C88—C87—H87A | 111 |
C41—C46—C49 | 120 (1) | C88—C87—H87B | 111 |
C45—C46—C49 | 119 (1) | H87A—C87—H87B | 109 |
C42—C47—H47A | 109 | O15—C88—C87 | 106 (1) |
C42—C47—H47B | 109 | O15—C88—H88A | 110 |
C42—C47—H47C | 109 | O15—C88—H88B | 109 |
H47A—C47—H47B | 109 | C87—C88—H88A | 110 |
H47A—C47—H47C | 109 | C87—C88—H88B | 110 |
H47B—C47—H47C | 109 | H88A—C88—H88B | 109 |
C44—C48—H48A | 112 | O16—C89—C90 | 96 (1) |
C44—C48—H48B | 108 | O16—C89—H89A | 112 |
C44—C48—H48C | 108 | O16—C89—H89B | 112 |
H48A—C48—H48B | 110 | C90—C89—H89A | 113 |
H48A—C48—H48C | 111 | C90—C89—H89B | 112 |
H48B—C48—H48C | 105 | H89A—C89—H89B | 108 |
C46—C49—H49A | 109 | C89—C90—C91 | 97 (1) |
C46—C49—H49B | 109 | C89—C90—H90A | 111 |
C46—C49—H49C | 109 | C89—C90—H90B | 112 |
H49A—C49—H49B | 110 | C91—C90—H90A | 111 |
H49A—C49—H49C | 109 | C91—C90—H90B | 113 |
H49B—C49—H49C | 109 | H90A—C90—H90B | 109 |
O8—C50—C27 | 122 (1) | C90—C91—C92 | 119 (2) |
O8—C50—C51 | 115 (1) | C90—C91—H91A | 107 |
C27—C50—C51 | 122 (1) | C90—C91—H91B | 106 |
C50—C51—H51A | 109 | C92—C91—H91A | 107 |
C50—C51—H51B | 108 | C92—C91—H91B | 106 |
C50—C51—H51C | 110 | H91A—C91—H91B | 109 |
H51A—C51—H51B | 108 | O16—C92—C91 | 80 (1) |
H51A—C51—H51C | 110 | O16—C92—H92A | 117 |
H51B—C51—H51C | 109 | O16—C92—H92B | 115 |
C28—C52—H52A | 108 | C91—C92—H92A | 116 |
C28—C52—H52B | 109 | C91—C92—H92B | 115 |
C28—C52—H52C | 109 | H92A—C92—H92B | 109 |
Co3—N17—C24—C25 | 35 (1) | N19—C56—C57—N20 | −51 (1) |
Co3—N17—C24—C32 | 164.3 (8) | N19—C56—C57—C73 | 175 (1) |
Co3—N18—C25—C24 | 27 (1) | N19—C56—C64—C65 | 90 (1) |
Co3—N18—C25—C41 | 152.3 (8) | N20—C57—C56—C64 | 177 (1) |
Co4—N19—C56—C57 | 40.6 (10) | N20—C57—C73—C74 | −91 (1) |
Co4—N19—C56—C64 | 176.3 (8) | N20—C57—C73—C78 | 85 (1) |
Co4—N20—C57—C56 | 41.5 (9) | C24—C25—C41—C42 | 71 (1) |
Co4—N20—C57—C73 | 178.8 (8) | C24—C25—C41—C46 | −109 (1) |
N17—C24—C25—N18 | −38 (1) | C25—C24—C32—C33 | −113 (1) |
N17—C24—C25—C41 | −163.8 (10) | C25—C24—C32—C37 | 70 (1) |
N17—C24—C32—C33 | 121 (1) | C56—C57—C73—C74 | 37 (1) |
N17—C24—C32—C37 | −54 (1) | C56—C57—C73—C78 | −145 (1) |
N18—C25—C24—C32 | −168.0 (10) | C57—C56—C64—C65 | −143 (1) |
N18—C25—C41—C42 | −48 (1) | C57—C56—C64—C69 | 35 (1) |
N18—C25—C41—C46 | 130 (1) | C64—C56—C57—C73 | 44 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9A···O7i | 0.95 | 1.94 | 2.69 (2) | 135 |
O9—H9B···O8ii | 0.96 | 2.56 | 2.74 (2) | 91 |
O14—H14A···O12iii | 0.95 | 1.73 | 2.67 (2) | 169 |
O14—H14B···O13iv | 0.96 | 1.97 | 2.73 (2) | 134 |
C40—H40A···N17 | 0.94 | 2.48 | 3.15 (2) | 128 |
C47—H47B···N18 | 0.95 | 2.45 | 3.09 (2) | 125 |
C29—H29A···O7 | 0.96 | 2.11 | 2.82 (2) | 130 |
C52—H52C···O8 | 0.94 | 2.07 | 2.78 (2) | 132 |
C47—H47B···O9 | 0.95 | 2.49 | 3.40 (2) | 159 |
C61—H61A···O12 | 0.94 | 1.91 | 2.69 (2) | 139 |
C84—H84C···O13 | 0.96 | 1.89 | 2.70 (2) | 139 |
C40—H40A···Br1 | 0.94 | 2.83 | 3.72 (2) | 157 |
C56—H56···Br2 | 0.95 | 2.89 | 3.44 (1) | 118 |
C68—H68···Br1i | 0.94 | 2.93 | 3.78 (2) | 151 |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x, y−1/2, −z+1; (iii) −x, y−1/2, −z+2; (iv) −x, y+1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [CoBr(C32H38N2O4)(H2O)]·C4H8O |
Mr | 743.62 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 297 |
a, b, c (Å) | 13.667 (2), 15.046 (2), 17.764 (2) |
β (°) | 100.32 (1) |
V (Å3) | 3593.8 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.64 |
Crystal size (mm) | 0.5 × 0.3 × 0.1 |
Data collection | |
Diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | Integration (Coppens et al., 1965) |
Tmin, Tmax | 0.619, 0.854 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12278, 11744, 6371 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.186, 1.04 |
No. of reflections | 11744 |
No. of parameters | 749 |
No. of restraints | ? |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.70, −0.60 |
Absolute structure | Flack (1983), 3169 Friedel pairs |
Absolute structure parameter | 0.04 (2) |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.
Br1—Co3 | 2.345 (2) | Co3—N18 | 1.88 (1) |
Br2—Co4 | 2.359 (3) | Co4—O10 | 1.89 (1) |
Co3—O5 | 1.91 (1) | Co4—O11 | 1.89 (1) |
Co3—O6 | 1.89 (1) | Co4—O14 | 1.997 (9) |
Co3—O9 | 2.007 (8) | Co4—N19 | 1.88 (1) |
Co3—N17 | 1.85 (1) | Co4—N20 | 1.87 (1) |
Br1—Co3—O9 | 178.6 (4) | Br2—Co4—O14 | 178.6 (4) |
N17—C24—C25—N18 | −38 (1) | N19—C56—C57—N20 | −51 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9A···O7i | 0.95 | 1.94 | 2.69 (2) | 135 |
O9—H9B···O8ii | 0.96 | 2.56 | 2.74 (2) | 91 |
O14—H14A···O12iii | 0.95 | 1.73 | 2.67 (2) | 169 |
O14—H14B···O13iv | 0.96 | 1.97 | 2.73 (2) | 134 |
C40—H40A···N17 | 0.94 | 2.48 | 3.15 (2) | 128 |
C47—H47B···N18 | 0.95 | 2.45 | 3.09 (2) | 125 |
C29—H29A···O7 | 0.96 | 2.11 | 2.82 (2) | 130 |
C52—H52C···O8 | 0.94 | 2.07 | 2.78 (2) | 132 |
C61—H61A···O12 | 0.94 | 1.91 | 2.69 (2) | 139 |
C84—H84C···O13 | 0.96 | 1.89 | 2.70 (2) | 139 |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x, y−1/2, −z+1; (iii) −x, y−1/2, −z+2; (iv) −x, y+1/2, −z+2. |
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The space group of the title CoIII complex, (I), is chiral since it was prepared with an optically pure tetradentate ligand. Pseudo-systematic absences h0l, l odd, were observed, which corresponds to the fact that the crystal structure has a pseudo-center of symmetry and the space group is approximately P21/c. However, both of the two independent Co complexes have the chiral ligand in an R,R configuration, as shown in Figs. 1 and 2, and there is no disorder around the asymmetric C atoms (C24, C25, C56, and C57). Although the values of the s.u.'s of coordinates are relatively high, the geometry is quite normal (Table 1).
Flack & Bernardinelli (1999) formulated the inversion-distinguishing power, which is not decreased by the pseudo-centrosymmetric arrangement of the heavy atoms if the light-atom substructure is clearly non-centrosymmetric. The title crystal is just the case and the absolute structure could be determined definitely based on Flack parameter, 0.04 (2). As seen from Fig. 3, the aromatic rings bonded at asymmetric C atoms contribute to the non-centrosymmetry.
There are intermolecular O—H···O hydrogen bonds involving the aqua ligands. The structures of the complex molecules have significant C—H···O close contacts (Table 2).